Extraction, Chemical Compositions and Biological Activities of Essential Oils of Cinnamomum verum Cultivated in Vietnam
1
Faculty of Biology, Thai Nguyen University of Education, Thai Nguyen City 24000, Vietnam
2
Faculty of Chemistry, Thai Nguyen University of Education, Thai Nguyen City 24000, Vietnam
3
Institute of Applied Technology and Sustainable Development, Nguyen Tat Thanh University, Ho Chi Minh City 700000, Vietnam
*
Authors to whom correspondence should be addressed.
Processes 2022, 10(9), 1713; https://0-doi-org.brum.beds.ac.uk/10.3390/pr10091713
Submission received: 29 July 2022
/
Revised: 23 August 2022
/
Accepted: 24 August 2022
/
Published: 28 August 2022
Abstract
:Cinnamomum verum (Cinnamomum genus) essential oil is commonly used in food preparation and traditional medicines, with a broad spectrum of biological activities. However, research on the extraction of essential oils (EOs) from C. verum cultivated locally in Vietnam is currently limited. Therefore, in this study, the chemical compositions and bioactivities of EOs from the bark and leaves of C. verum collected from the Thai Nguyen and Yen Bai provinces of Vietnam were investigated. The EOs samples were extracted by using water distillation, organic solvent (n-hexane) and ultrasound-assisted (in n-hexane solvent) extraction methods. The chemical composition of the obtained EOs were analyzed by GC-FID and GC/MS analyses. Results showed that the major chemical compositions of C. verum EOs were: (E)-cinnamaldehyde, trans-cinnamic acid, cinnamyl acetate, and benzaldehyde. Furthermore, C. verum EOs exhibited inhibitory activities against two tested cancer cell lines and four bacterial strains. These findings provide essential knowledge about the potential application of C. verum EOs cultivated in Vietnam for the pharmaceutical industry.
1. Introduction
The Cinnamomum genus consists of various tropical plants which originated and are widely cultivated in Southeast Asia [1]. The essential oils (EOs), enriched in the aromatic bark and leaves of the plants, are commonly used as a spice in food and as a traditional remedy for colds, flatulence, control of blood sugar levels, anti-aging, muscle and menstrual-related pain [2]. The chemical components of cinnamon EOs have been of significant interest. To date, a total of 43 monoterpenes, 83 sesquiterpenoids, and 55 diterpenes have been reported, with major components being cinnamaldehyde, cinnamyl acetate, cinnamic acid, eugenol, and linalool, thus, giving rise to a wide range of biological activities such as anti-microorganism, antioxidant, anti-biofilm, and anti-cancer [3,4,5,6,7].
Cinnamomum verum (C. verum) is an important spice of the Cinnamomum genus, whose bark is commonly used as a spice product [8]. C. verum has also been used as (1) an insulin receptor for diabetes treatments, and (2) an enhancer for the activation of glycogen synthase and inhibition of glycation against the multi-drug resistant strains of clinical Shigella [9,10,11,12]. The EOs of C. verum have been shown to exhibit anti-bacterial and anti-biofilm activities against Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella pneumoniae (MIC = 0.5 mg/mL and MBC = 1.0 mg/mL) by targeting the bacterial cell wall and reducing biofilm density while not exerting any toxicity to human keratinocytes [13]. Similar results were obtained upon the application of C. verum bark EOs against multidrug-resistant Escherichia coli (E. coli) strains, in which the bacterial cell membrane permeability and expression of quorum sensing, biofilm formation and zinc homeostasis were suppressed [14,15]. In addition, C. verum EOs exhibited in vitro and in vivo anti-cancer activity against hepatocellular carcinoma sK-Hep-1 cells, human colorectal adenocarcinoma COLO 205 cells, and lung adenocarcinoma A549 cells, evaluated by using anti-topoisomerase I and II [16,17,18]. The broad spectrum of anti-microorganism, anti-biofilm and anti-cancer actions of C. verum EOs are derived from the diversified phytochemical profile, predominantly cinnamaldehyde [19,20].
To date, the chemical composition of EOs derived from C. verum leaves and bark cultivated in Vietnam, as well as their anti-cancer and anti-bacterial activities, have been the subject of limited research. Therefore, we sought to isolate the EOs from leaves and bark of C. verum collected in Vietnam, followed by the identification of their chemical compositions, and investigation of their inhibitory activities against various bacteria and cancer cell lines.
2. Materials and Methods
2.1. Preaparation of Plant Materials, Chemicals and Reagents
The bark and leaves of C. verum (300 g) were collected under conditions of 28 °C, 85% relative humidity, and photoperiods of 9 h in Thai Nguyen (21.5672° N and 105.8252° E) and Yen Bai (21.7168° N and 104.8986° E) provinces, Vietnam, during February 2020. The samples were authenticated by Dr. S.D. Thuong, Department of Biology, Thai Nguyen University of Education (TNUE), Vietnam. C. verum samples were fragmented into small pieces sized about 1–2 cm and stored in the refrigerator between 2 and 5 °C for EOs extraction using water distillation, organic solvent (n-hexane) and ultrasound-assisted extraction methods [5,21,22].
n-hexane, ampicillin, ellipticine and (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) were purchased from Sigma-Aldrich Co. (St. Louis, MO, U.S.A.), all of analytical grade.
2.2. EOs Extraction
The water distillation extraction procedure of C. verum bark EOs was performed as previously described by Dao et al. (2022) [21], which employed a Clevenger device under 1000 W of heating capacity and 1.5 h of extraction time. The upper layer of EOs was collected and stored in sealed vials at 4 °C until use.
The ultrasound-assisted (in n-hexane solvent) extraction procedure of C. verum bark EOs was performed as previously described by Anton et al. (2022) [22]. Briefly, the sample was added into a reflux extractor with an aqueous condenser and a 500 mL glass flask. Then, 300 mL of n-hexane (Merck) was added into the 500 mL glass flask of the reflux extractor and placed in an ultrasonic bath. Extraction conditions were at 40 °C, frequency 25 kHz, extraction time 1.5 h [21]. The n-hexane EOs extract was filtered by using a syringe filter (0.25 μm in diameter). n-hexane was recovered under reduced pressure (100–150 mbar) at a temperature of 25 °C to obtain the EOs, which were then stored at 4 °C until use.
The organic extraction (n-hexane) extraction procedure of C. verum bark EOs was performed as previously described by Setyowati et al. (2022) [23]. Samples were mixed with 300 mL of n-hexane in a 500 mL glass flask, and extraction was performed at room temperature for 12 h. The n-hexane extract was filtered using a syringe filter (0.25 μm in diameter). n-hexane was recovered under 100–150 mbar and 25 °C to obtain the EOs samples, which were then stored at 4 °C until use.
2.3. GC-FID and GC-MS Analysis of EOs
The identification of chemical components of extracted EOs involved the use of an Agilent Technologies 6890N (U.S.A.) system with AHP5-MS column (30 m × 0.25 mminternal diameter, film thickness 0.25 µm) with an FID in the condition helium (0.9 mL/min) as a carrier gas, and connected by a mass spectrometer HP 5973 MSD. Chemical compositions of the samples have been confirmed by comparison with the relative retention indices (RI) reference and the National Institute of Standards and Technology (NIST) library [24,25,26].
2.4. MTT and MIC Assays
The anti-cancer activity of C. verum bark EOs, against human liver (HepG2) and breast cancer cell lines (MCF-7), was determined by using the MTT method with slight modifications [27,28]. In brief, the cells obtained from the American Type Culture Collection (ATCC, Manassas, VA, U.S.A.) were seeded in a 96-well plate with a destiny of 2.5 × 103 cells/well and incubated for 12 h. Cells were treated in triplicate with C. verum bark EOs samples from Thai Nguyen and Yen Bai provinces at a concentration of 100 μg/mL for 24 h (37 °C, 5% CO2, and 90% humidity). Then, 20 µL of MTT (0.5 mg/mL) was added and the plate was incubated for another 4 h at 37 °C. Then, 200 µL of lysis buffer, which consisted of 5% isobutyl alcohol, 10% SDS, and 0.012 mol/L of HCl, was added to dissolve the residues. The optical density (OD) was measured at 595 nm using a UV-Vis 1200 Spectrophotometer (Shimadzu, Japan). The IC50 (half-maximal inhibitory concentration) was calculated by using the logarithmic method.
Minimum inhibitory concentration (MIC) assay was used to determine the anti-bacterial activity of C. verum bark EOs against Bacillus subtilis ATCC 6633, Escherichia coli ATCC 25922, E. coli, Sarcina lutea ATCC 9341, and Lactobacillus plantarum obtained from ATCC (Manassas, VA, U.S.A.), as described in previous studies [29,30,31]. Briefly, the fresh cell cultures of four bacterial strains were grown in Mueller Hinton Broth (MHB), adjusted to 0.5 McFarland standard in NaCl 0.9% solution (w/v) and added to a 96-well plate (3 × 104 colony forming units/mL). Then, C. verum bark EOs samples from Thai Nguyen and Yen Bai provinces at a concentration of 100 μg/mL (100 mg/mL stock prepared in DMSO) were added to the plate. The plate was then incubated under agitation (120 rpm) at 37 °C for 24 h. Ampicillin in MHB (10 μg/mL) and MHB were used as a positive and negative control, respectively. After incubation, OD measurement was carried out at a wavelength of 600 nm using a UV-Vis 1200 Spectrophotometer (Shimadzu, Japan). The experiment was repeated three times and the results were represented as mean ± standard deviation (S.D.).
2.5. Statistical Analysis
All data in the present study were obtained from two-way ANOVA and were represented as mean ± standard deviation, with p-value < 0.05 being considered as statistical difference.
3. Results
EOs were extracted from C. verum bark by using different extraction methods, including n-hexane solvent, water distillation and ultrasound-assisted extraction, to afford EOs yields of 2.32%, 1.42%, and 1.05%, respectively. The results showed that the extraction effectiveness was higher when using organic solvents, than water distillation or ultrasound-assisted extraction. However, the chemical components of EOs extracted from water distillation were more diverse than ultrasound-assisted or organic solvent extraction. In addition, the major chemical compositions of EOs obtained from water distillation, including (E)-cinnamaldehyde, cinnamyl acetate, and trans- and cis-cinnamic acid, were present at a comparatively high level, of 61.531%, 15.512%, 0.437%, 1.022% and 6.401%, respectively, as compared with the other two methods (Table 1). This result was in contrast to previous works in which the ultrasonic-assisted method, through a liquid medium, reduced the processing time, solvent and energy consumption for the selective extraction of target compounds [32]. Such difference can be explained by the fact that the C. verum grown in Vietnam possesses a different oil content and phytochemical profile that can be well-maintained by water distillation extraction. Overall, the EOs obtained from water distillation of C. verum grown in Vietnam were suitable for subsequent analyses, due to comparative oil yield and quality.
Subsequently, the starting materials (i.e., leaves and bark) collected from Thai Nguyen and Yen Bai provinces were investigated for EOs extraction efficiency and chemical composition by using the water distillation method. The chemical constituents of the EOs samples are illustrated in Table 2 and Table 3, as well as Figure 1 and Figure 2. Both leaves and bark EOs samples contained a high content of (E)-Cinnamaldehyde (43.446–61.531%). Specifically, (E)-Cinnamaldehyde in C. verum bark EOs collected in Yen Bai province had the highest content of 61.531%, which was higher than C. zeylanicum Blume bark (57.73 ± 1.64%), but lower than C. cassia Presl. samples from China (85.06–89.95%) and C. verum from Morocco (89.31%) [20,33,34,35]. Additionally, several components were discovered for the first time in the leaves and bark of C. verum, such as 3,4-dihydro-1(2H)-naphthalenone, isoaromadendrene epoxide, (E)- 3-(2-hydroxyphenyl)- 2-Propenoic acid, and 1,4-diphenyl-1,4-Butanedione. This result was in close agreement with previous studies and indicated that geographical distribution plays a significant role in the plant’s chemical composition and biological activity [5,13,20].
Numerous studies have reported that the chemical compositions of EOs extracted from Cinnamon plants exhibited a wide range of biological activities, including antioxidant, anti-microbial and anti-cancer activities [13,14,15,16,17,18,19,20]. In this work, we evaluated the anti-microbial activities against four bacterial strains, as well as anti-cancer activity against HepG2 and MCF-7, of C. verum bark EOs collected in Thai Nguyen and Yen Bai provinces (Vietnam) by the water distillation method. The results are summarized in Table 4 and Table 5.
Results of anti-microbial activities of C. verum EOs are presented in Table 4, in which the EOs extracted from C. verum bark exhibited average anti-bacterial activity. In particular, the sample collected from Yen Bai had higher anti-bacterial activity than the Thai Nguyen sample. The anti-bacterial activity of the sample collected in Yen Bai and Thai Nguyen provinces of Vietnam, against the E. coli strain, was indicated by MIC = 115.6 and 135.4 μg/mL, respectively, which were higher than for the sample collected in Morocco (MIC = 265.44 μg/mL) [20], as the chemical compositions of this species can be varied depending on the geographical distribution. The significant inhibitory action of the obtained C. verums bark EOs against a broad spectrum of Gram-positive and Gram-negative food-spoilage bacteria can be explained by the high content of cinnamaldehyde [36,37]. The compound has been reported to mainly target (1) the cell wall permeability, (2) cytoplasmic proteins, as well as (3) glycerophospholipid-encoded genes expression and glycerophospholipid biosynthesis pathway, thereby altering their growth, energy production and metabolism [38,39,40].
As shown in Table 5, the EOs extract from the bark of C. verum also exhibited inhibitory activities against proliferation in both cancer cell lines. The sample collected from Thai Nguyen province exhibited higher anti-cancer activities than the sample collected from Yen Bai province. Results showed that EOs extracted from C. verum bark in Vietnam displayed inhibitory activity against proliferation in HepG2 cells due to the high content of cinnamaldehyde, cinnamic acid and cinnamyl alcohol, which have previously been shown to be able to down-regulate proteins expression and pathways, thus, promoting tumor cell apoptosis [41,42,43,44,45]. The toxicity of the obtained C. verum bark EOs against the proliferation of MCF-7 (as indicated by the IC50 value) in the present study was lower than the methanolic extract of C. zeylanicum [46]. Overall, the EOs extract from C. verum bark by water distillation exhibited anti-bacterial and anti-cancer activities, which were derived from the valuable phytochemical content.
4. Conclusions
The composition of EOs extracted from different parts of C. verum collected in Vietnam were analyzed by GC-FID and GC/MS systems. Results have shown that compared with solvent extraction and ultrasound-assisted extraction, the extraction of EOs from C. verum bark by the water distillation method produced a comparative oil yield (1.42%) with a high content of (E)-Cinnamaldehyde (61.531%) and (Z)- and (E)-cinnamyl acetate, as well as trans- and cis-cinnamic acid. Furthermore, the obtained EOs also exhibited various inhibitory activity against proliferation in two cancer cell lines and four bacterial strains, thus, can be regarded as a potential natural-based agent for the pharmaceutical industry.
Author Contributions
Conceptualization, H.H.P. and K.P.V.; methodology, H.H.P., K.P.V. and T.H.T.; software, H.H.P.; investigation, T.H.T.; writing—original draft preparation, H.H.P. and K.P.V.; writing—review and editing, H.H.P., T.H.T. and D.T.N.P.; supervision, K.P.V. and T.H.T. All authors have read and agreed to the published version of the manuscript.
Funding
This work was financially supported by the Thai Nguyen University of Education CS.2021.18.
Institutional Review Board Statement
Not applicable.
Informed Consent Statement
Not applicable.
Data Availability Statement
Not applicable.
Acknowledgments
This paper is based upon work supported by the Science, Technology and Innovation Funding Authority (STDF) under grant (30102).
Conflicts of Interest
The authors declare no conflict of interest.
References
- Barceloux, D.G. Cinnamon (Cinnamomum Species). Dis.-A-Mon. 2009, 55, 327–335. [Google Scholar] [CrossRef]
- Wu, M.; Ni, L.; Lu, H.; Xu, H.; Zou, S.; Zou, X. Terpenoids and Their Biological Activities from Cinnamomum: A Review. J. Chem. 2020, 2020, 1–14. [Google Scholar] [CrossRef]
- Balijepalli, M.K.; Buru, A.S.; Sakirolla, R.; Pichika, M.R. Cinnamomum genus: A review on its biological activities. Int. J. Pharm. Pharm. Sci. 2017, 9, 1–11. [Google Scholar]
- Zhao, J.; Ma, J.S. Phytochemicals and biological activities of the genus Cinnamomum. Res. Rev. J. Pharmacogn. Phytochem. 2016, 4, 27–34. [Google Scholar]
- Kumar, S.; Kumari, R.; Mishra, S. Pharmacological Properties and Their Medicinal Uses of Cinnamomum: A Review. J. Pharm. Pharmacol. 2019, 71, 1735–1761. [Google Scholar] [CrossRef]
- Firmino, D.F.; Cavalcante, T.T.A.; Gomes, G.A.; Firmino, N.C.S.; Rosa, L.D.; de Carvalho, M.G.; Catunda Jr, F.E.A. Antibacterial and Antibiofilm Activities of Cinnamomum Sp. Essential Oil and Cinnamaldehyde: Antimicrobial Activities. Sci. World J. 2018, 2018, 1–9. [Google Scholar] [CrossRef] [PubMed]
- Shreaz, S.; Wani, W.A.; Behbehani, J.M.; Raja, V.; Irshad, M.; Karched, M.; Ali, I.; Siddiqi, W.A.; Hun, L.T. Cinnamaldehyde and its derivatives, a novel class of antifungal agents. Fitoterapia 2016, 112, 116–131. [Google Scholar]
- Chakraborty, S.; Dutta, H. Use of Nature-derived Antimicrobial Substances as Safe Disinfectants and Preservatives in Food Processing Industries: A Review. J. Food Process. Preserv. 2021, 00, e15999. [Google Scholar] [CrossRef]
- Shori, A.B.; Baba, A.S. Cinnamomum Verum Improved the Functional Properties of Bioyogurts Made from Camel and Cow Milks. J. Saudi Soc. Agric. Sci. 2011, 10, 101–107. [Google Scholar] [CrossRef]
- Jiménez-Redondo, N.; Vargas, A.E.; Teruel-Andreu, C.; Lipan, L.; Muelas, R.; Hernández-García, F.; Sendra, E.; Cano-Lamadrid, M. Evaluation of Cinnammon (Cinnamomum cassia and Cinnamomum verum) Enriched Yoghurt during Refrigerated Storage. LWT 2022, 159, 113240. [Google Scholar] [CrossRef]
- Khawsud, A.; AumpaFord, P.; Junsi, M.; Jannu, T.; Nortuy, N.; Sukeaw Samakradhamrongthai, R. Effect of black pepper (Piper nigrum) and cinnamon (Cinnamomum verum) on properties of reduced− fat milk− based ice cream. Food Appl. Biosci. J. 2020, 8, 54–67. [Google Scholar]
- Qais, F.A.; Sarwar, T.; Ahmad, I.; Khan, R.A.; Shahzad, S.A.; Husain, F.M. Glyburide Inhibits Non-Enzymatic Glycation of HSA: An Approach for the Management of AGEs Associated Diabetic Complications. Int. J. Biol. Macromol. 2021, 169, 143–152. [Google Scholar] [CrossRef] [PubMed]
- Wijesinghe, G.K.; Feiria, S.B.; Maia, F.C.; Oliveira, T.R.; Joia, F.; Barbosa, J.P.; Boni, G.C.; Höfling, J.F. In-vitro antibacterial and antibiofilm activity of Cinnamomum verum leaf oil against Pseudomonas aeruginosa, Staphylococcus aureus and Klebsiella pneumoniae. An. Acad. Bras. Ciênc. 2021, 93, e20201507. [Google Scholar] [CrossRef] [PubMed]
- Yap, P.S.X.; Krishnan, T.; Chan, K.G.; Lim, S.H.E. Antibacterial Mode of Action of Cinnamomum Verum Bark Essential Oil, Alone and in Combination with Piperacillin, Against a Multi-Drug-Resistant Escherichia Coli Strain. J. Microbiol. Biotechnol. 2015, 25, 1299–1306. [Google Scholar] [CrossRef] [PubMed]
- Cherng, J.M.; Perng, D.S.; Tsai, Y.H.; Cherng, J.; Scotti, R.W.; Stringaro, A.; Nicolini, L.; Zanellato, M.; Boccia, P.; Maggi, F.; et al. Effects of Essential Oils from Cymbopogon spp. and Cinnamomum verum on Biofilm and Virulence Properties of Escherichia coli O157:H7. Antibiotics 2021, 10, 113. [Google Scholar] [CrossRef]
- Cherng, J.-M.; Perng, D.-S.; Tsai, Y.-H.; Cherng, J.; Wang, J.-S.; Chou, K.-S.; Shih, C.-W. Discovery of a Novel Anticancer Agent with Both Anti-Topoisomerase I and II Activities in Hepatocellular Carcinoma SK-Hep-1 Cells in Vitro and in Vivo: Cinnamomum verum Component 2-Methoxycinnamaldehyde. DDDT 2016, 10, 141. [Google Scholar] [CrossRef]
- Tsai, K.; Liu, Y.-H.; Chen, T.-W.; Yang, S.-M.; Wong, H.-Y.; Cherng, J.; Chou, K.-S.; Cherng, J.-M. Cuminaldehyde from Cinnamomum verum Induces Cell Death through Targeting Topoisomerase 1 and 2 in Human Colorectal Adenocarcinoma COLO 205 Cells. Nutrients 2016, 8, 318. [Google Scholar] [CrossRef]
- Wong, H.; Tsai, K.; Liu, Y.; Yang, S.; Chen, T.; Cherng, J.; Chou, K.; Chang, C.; Yao, B.; Cherng, J. Cinnamomum verum component 2-methoxycinnamaldehyde: A novel anticancer agent with both anti-topoisomerase I and II activities in human lung adenocarcinoma a549 cells in vitro and in vivo. Phytother Res. 2016, 30, 331–340. [Google Scholar] [CrossRef]
- Singh, N.; Rao, A.S.; Nandal, A.; Kumar, S.; Yadav, S.S.; Ganaie, S.A.; Narasimhan, B. Phytochemical and Pharmacological Review of Cinnamomum Verum J. Presl-a Versatile Spice Used in Food and Nutrition. Food Chem. 2021, 338, 127773. [Google Scholar] [CrossRef]
- Ainane, T.; Khammour, F.; Merghoub, N.; Elabboubi, M.; Charaf, S.; Ainane, A.; Elkouali, M.H.; Talbi, M.; Abba, E.H.; Cherroud, S. Cosmetic Bio-Product Based on Cinnamon Essential Oil “Cinnamomum verum” for the Treatment of Mycoses: Preparation, Chemical Analysis and Antimicrobial Activity. MOJT 2019, 5, 5–8. [Google Scholar] [CrossRef]
- Dao, T.P.; Tran, N.Q.; Tran, T.T.; Lam, V.T. Assessing the Kinetic Model on Extraction of Essential Oil and Chemical Composition from Lemon Peels (Citrus aurantifolia) by Hydro-Distillation Process. Mater. Today: Proc. 2022, 51, 172–177. [Google Scholar] [CrossRef]
- Anton, A.; Rob, G.; Matthias, W.; Mirko, S.; Bjorn, G.; Jeroen, J.; Jinu, J.; Tom, V. Ultrasound-assisted emerging technologies for chemical processes. J. Chem. Technol. Biotechnol. 2018, 93, 1219–1227. [Google Scholar] [CrossRef]
- Setyowati, F.P.; Utami, R.; Khasanah, L.U.; Manuhara, G.J. Optimization of Two-Stage Cinnamon Bark (Cinnamomum burmanii) Oleoresin Maceration Extraction Process with Ethanol Solvent Using Response Surface Methodology (RSM). In AIP Conference Proceedings; AIP Publishing LLC: Geneva, Switzerland, 2018; p. 020072. [Google Scholar]
- Doukkali, E.; Radouane, N.; Tahiri, A.; Tazi, B.; Guenoun, F.; Lahlali, R. Chemical Composition and Antibacterial Activity of Essential Oils of Cinnamomum cassia and Syzygium aromaticum Plants and Their Nanoparticles against Erwinia Amylovora. Arch. Phytopathol 2022, 55, 217–234. [Google Scholar] [CrossRef]
- Kačániová, M.; Galovičová, L.; Valková, V.; Tvrdá, E.; Terentjeva, M.; Žiarovská, J.; Kunová, S.; Savitskaya, T.; Grinshpan, D.; Štefániková, J.; et al. Antimicrobial and Antioxidant Activities of Cinnamomum cassia Essential Oil and Its Application in Food Preservation. Open Chem. 2021, 19, 214–227. [Google Scholar] [CrossRef]
- Sparkman, O.D. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy Robert P. Adams. J. Am. Soc. Mass. Spectrom. 2005, 16, 1902–1903. [Google Scholar] [CrossRef]
- Ahamad, J.; Uthirapathy, S.; Mohammed Ameen, M.S.; Anwer, E.T. Essential Oil Composition and Antidiabetic, Anticancer Activity of Rosmarinus officinalis L. Leaves from Erbil (Iraq). J. Essent. Oil-Bear. Plants 2019, 22, 1544–1553. [Google Scholar] [CrossRef]
- Van Khang, P.; Hu, L.; Ma, L. One-Pot Synthesis of Isoindolin-1-Ones with Thiamine Hydrochloride (VB 1) as a Catalyst and Their Inhibitory Activity Against Cancer Cell Lines. Polycycl. Aromat. Compd. 2020, 40, 33–39. [Google Scholar] [CrossRef]
- Wiegand, I.; Hilpert, K.; Hancock, R. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat. Protoc. 2008, 3, 163–175. [Google Scholar] [CrossRef]
- Elgammal, E.; El Gendy, A.E.N.; Elgamal, A.E.-B. Mechanism of Action and Bioactivities of Cinnamomum zeylanicum Essential Oil against Some Pathogenic Microbes. Egypt Pharmaceut. J. 2020, 19, 162. [Google Scholar] [CrossRef]
- Coimbra, A.; Ferreira, S.; Duarte, A.P. Biological Properties of Thymus zygis Essential Oil with Emphasis on Antimicrobial Activity and Food Application. Food Chem. 2022, 393, 133370. [Google Scholar] [CrossRef]
- Jain, P.L.B.; Patel, S.R.; Desai, M.A. An Innovative Ultrasonic-Assisted Extraction Process for Enhancing the Patchoulol from Pogostemon cablin Essential Oil Using Hydrotropes. Mater. Today Proc. 2022, 57, 2377–2380. [Google Scholar] [CrossRef]
- Ooi, L.S.M.; Li, Y.; Kam, S.-L.; Wang, H.; Wong, E.Y.L.; Ooi, V.E.C. Antimicrobial Activities of Cinnamon Oil and Cinnamaldehyde from the Chinese Medicinal Herb Cinnamomum cassia Blume. Am. J. Chin. Med. 2006, 34, 511–522. [Google Scholar] [CrossRef] [PubMed]
- Nwanade, C.F.; Wang, M.; Wang, T.; Zhang, X.; Wang, C.; Yu, Z.; Liu, J. Acaricidal Activity of Cinnamomum Cassia (Chinese Cinnamon) against the Tick Haemaphysalis longicornis Is Linked to Its Content of (E)-Cinnamaldehyde. Parasites Vectors 2021, 14, 330. [Google Scholar] [CrossRef]
- Huang, Z.; Pang, D.; Liao, S.; Zou, Y.; Zhou, P.; Li, E.; Wang, W. Synergistic Effects of Cinnamaldehyde and Cinnamic Acid in Cinnamon Essential Oil against S. Pullorum. Ind. Crops Prod. 2021, 162, 113296. [Google Scholar] [CrossRef]
- Zhang, Y.; Liu, X.; Wang, Y.; Jiang, P.; Quek, S. Antibacterial activity and mechanism of cinnamon essential oil against Escherichia coli and Staphylococcus aureus. Food Control 2016, 59, 282–289. [Google Scholar] [CrossRef]
- He, Z.; Huang, Z.; Jiang, W.; Zhou, W. Antimicrobial Activity of Cinnamaldehyde on Streptococcus Mutans Biofilms. Front. Microbiol. 2019, 10, 2241. [Google Scholar] [CrossRef]
- Doyle, A.A.; Stephens, J.C. A Review of Cinnamaldehyde and Its Derivatives as Antibacterial Agents. Fitoterapia 2019, 139, 104405. [Google Scholar] [CrossRef]
- Gill, A.O.; Holley, R.A. Mechanisms of Bactericidal Action of Cinnamaldehyde against Listeria Monocytogenes and of Eugenol against Listeria monocytogenes and Lactobacillus sakei. Appl. Environ. Microbiol. 2004, 70, 5750–5755. [Google Scholar] [CrossRef]
- Pang, D.; Huang, Z.; Li, Q.; Wang, E.; Liao, S.; Li, E.; Zou, Y.; Wang, W. Antibacterial Mechanism of Cinnamaldehyde: Modulation of Biosynthesis of Phosphatidylethanolamine and Phosphatidylglycerol in Staphylococcus aureus and Escherichia coli. J. Agric. Food Chem. 2021, 69, 13628–13636. [Google Scholar] [CrossRef]
- Liu, Y.; An, T.; Wan, D.; Yu, B.; Fan, Y.; Pei, X. Targets and Mechanism Used by Cinnamaldehyde, the Main Active Ingredient in Cinnamon, in the Treatment of Breast Cancer. Front. Pharmacol. 2020, 11, 582719. [Google Scholar] [CrossRef]
- Lin, L.-T.; Wu, S.-J.; Lin, C.-C. The Anticancer Properties and Apoptosis-Inducing Mechanisms of Cinnamaldehyde and the Herbal Prescription Huang-Lian-Jie-Du-Tang (黃連解毒湯 Huáng Lián Jiě Dú Tang) in Human Hepatoma Cells. eJTCM 2013, 3, 227–233. [Google Scholar] [CrossRef]
- Dutta, A.; Chakraborty, A. Cinnamon in Anticancer Armamentarium: A Molecular Approach. J. Toxicol. 2018, 2018, 1–8. [Google Scholar] [CrossRef] [PubMed]
- Kostrzewa, T.; Przychodzen, P.; Gorska-Ponikowska, M.; Kuban-Jankowska, A. Curcumin and Cinnamaldehyde as PTP1B Inhibitors With Antidiabetic and Anticancer Potential. Anticancer. Res. 2019, 39, 745–749. [Google Scholar] [CrossRef] [PubMed]
- Mabeta, P.; Pavić, K.; Zorc, B. Insights into the Mechanism of Antiproliferative Effects of Primaquine-Cinnamic Acid Conjugates on MCF-7 Cells. Acta Pharmaceutica 2018, 68, 337–348. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Azmi, A.N.; Abd Wahab, W.; Md Zin, N.H.; Muhamad Bunnori, N.; Haron, N. The Investigation of Cytotoxic Effects of Cinnamomum zeylanicum on Human Breast Cancer Cell Line (MCF-7). IMJM 2020, 15. [Google Scholar] [CrossRef]
Figure 1.
GC-FID spectra of EOs extracted from C. verum leaves cultivated in Thai Nguyen and Yen Bai, with n-hexane used as the extraction solvent.
Figure 1.
GC-FID spectra of EOs extracted from C. verum leaves cultivated in Thai Nguyen and Yen Bai, with n-hexane used as the extraction solvent.
Figure 2.
GC-FID spectra of EOs extracted from C. verum bark cultivated in Thai Nguyen or Yen Bai, with n-hexane used as the extraction solvent.
Figure 2.
GC-FID spectra of EOs extracted from C. verum bark cultivated in Thai Nguyen or Yen Bai, with n-hexane used as the extraction solvent.
Table 1.
Chemical components of C. verum bark EOs extracted by different extraction methods.
| Components No. | Components | RI (Ref.) | RI (Exp.) | Water Distillation (%) | Organic Solvent (N-Heaxane) (%) | Ultrasound-Assisted Extraction (in N-Hexane) (%) |
|---|---|---|---|---|---|---|
| 1 | Benzaldehyde | 966 | 966 | 3.574 | 4.267 | 2.675 |
| 2 | Benzeneacetaldehyde | 1049 | 1049 | 2.667 | 1.554 | 2.667 |
| 3 | Acetophenone | 1068 | 1067 | 0.113 | - | - |
| 4 | Benzenepropanal | 1170 | 1169 | 1.093 | 1.342 | 0.846 |
| 5 | (Z)-3-Phenylacrylaldehyde | 1223 | 1224 | 1.345 | 1.012 | 1.042 |
| 6 | (E-)-Cinnamaldehyde | 1266 | 1267 | 61.531 | 58.345 | 57.464 |
| 7 | Hydrocinnamic acid | 1361 | 1361 | 0.162 | - | 0.873 |
| 8 | 3-phenyl-2-Propenoic acid | 1434 | 1433 | 0.223 | - | - |
| 9 | (Z)-Cinnamyl acetate | 1445 | 1445 | 15.512 | 13.412 | 11.674 |
| 10 | (E-)-Cinnamyl acetate | 1452 | 1453 | 0.437 | 0.545 | 0.465 |
| 11 | trans-Cinnamic acid | 1454 | 1455 | 1.022 | 1.894 | 1.453 |
| 12 | Cis-Cinnamic acid | 1463 | 1464 | 6.401 | 7.452 | 8.342 |
| 13 | (3-Phenyloxiran-2-yl) methyl acetate | 1502 | 1502 | 0.126 | 0.126 | 0.126 |
| 14 | 3-(2-methoxyphenyl)- 2-propenal | 1505 | 1505 | 0.099 | 0.106 | 0.567 |
| 15 | Tetradecanal | 1606 | 1607 | 0.110 | - | 0.310 |
| 16 | (E-)-3-(2-hydroxyphenyl)-2-propenoic acid | 1630 | 1631 | 0.245 | 0.178 | 0.104 |
| 17 | Chalcone | 1970 | 1971 | 0.118 | - | 0.223 |
| 18 | 1,4-diphenyl-1,4-butanedione | - | - | 0.595 | 0.234 | 0.605 |
| 19 | 5-Phenyl-2,4-pentadienophenone | - | - | 0.105 | 0.205 | - |
| 20 | α-Oxo-Benzeneacetonitrile | - | - | 0.177 | 0.232 | 0.154 |
| 21 | Sitosetrol | - | - | - | 2.345 | 3.456 |
| 22 | Beta-amyrin | - | - | - | 1.212 | 1.457 |
Table 2.
Chemical components of C. verum leaf EOs from different cultivation locations.
| Components No. | Components | RI (Ref.) | RI (Exp.) | % EOs from C. verum Leaves from Thai Nguyen Province | % EOs from C. verum Leaves from Yen Bai Province |
|---|---|---|---|---|---|
| 1 | Styrene | 890 | 890 | - | 0.115 |
| 2 | α-Pinene | 917 | 917 | - | 0.763 |
| 3 | Camphene | 952 | 951 | - | 1.097 |
| 4 | Benzaldehyde | 966 | 966 | 4.939 | 4.708 |
| 5 | Beta-Pinene | 980 | 980 | - | 0.389 |
| 6 | D-Limonene | 1027 | 1026 | - | 0.203 |
| 7 | 2-hydroxybenzaldehyde | 1041 | 1041 | 2.054 | 1.214 |
| 8 | Acetophenone | 1068 | 1067 | - | 0.163 |
| 9 | Phenylethyl Alcohol | 1116 | 1117 | - | 0.334 |
| 10 | endo-Borneol | 1166 | 1166 | - | 0.29 |
| 11 | Benzenepropanal | 1170 | 1169 | 2.781 | 1.694 |
| 12 | Benzeneacetic acid, methyl ester | 1187 | 1187 | 0.329 | |
| 13 | (Z)-3-Phenylacrylaldehyde | 1223 | 1223 | 1.962 | - |
| 14 | 3-methyl-3-(4-methyl-3-pentenyl) oxiranecarboxaldehyde | 1236 | 1236 | 0.778 | - |
| 15 | Benzenepropanenitrile | 1243 | 1243 | 2.345 | 5.746 |
| 16 | 2-phenylethyl acetate | 1256 | 1255 | - | 0.778 |
| 17 | (E)-Cinnamaldehyde | 1266 | 1266 | 44.955 | 43.446 |
| 18 | 1-phenyl-1,2-ethanediol | 1308 | 1307 | - | 0.302 |
| 19 | 8,9-dehydro cycloisolongifolene | 1311 | 1312 | 0.341 | - |
| 20 | [1S-(1α,2α,3aβ,4α,5α,7aβ,8S*)]- octahydro-1,7a-dimethyl-5-(1-methylethyl)-1,2,4-Metheno-1H-indene | 1364 | 1364 | - | 0.144 |
| 21 | Copaene | 1376 | 1376 | - | 0.551 |
| 22 | Hydroquinone acetate | 1383 | 1382 | 0.333 | 0.361 |
| 23 | (-)-β-Bourbonene | 1384 | 1385 | - | 0.557 |
| 24 | 3-phenyl-2-propenoic acid | 1434 | 1434 | 2.416 | 8.239 |
| 25 | (Z)-Cinnamyl acetate | 1445 | 1445 | 10.419 | 8.419 |
| 26 | 3,4-dihydro-1(2H)-naphthalenone | 1458 | 1457 | 6.795 | 3.675 |
| 27 | (Z)-2-Methoxycinnamaldehyde | 1463 | 1463 | 0.29 | - |
| 28 | γ-Muurolene | 1474 | 1472 | 0.763 | |
| 29 | cis-Calamenene | 1531 | 1532 | 0.134 | |
| 30 | (E)- 3,7,11-trimethyl-1,6,10-Dodecatrien-3-ol | 1551 | 1551 | 2.261 | 1.359 |
| 31 | [1ar-(1aα,4aα,7β,7aβ,7bα)]- decahydro-1,1,7-trimethyl-4-methylene-1H-Cycloprop[e]azulen-7-ol | 1571 | 1571 | 0.766 | - |
| 32 | Caryophyllene oxide | 1578 | 1578 | - | 0.575 |
| 33 | Isoaromadendrene epoxide | 1584 | 1583 | 2.041 | 1.045 |
| 34 | [1aR-(1aα,4β,4aβ,7α,7aβ,7bα)]- decahydro-1,1,4,7-tetramethyl-1H-Cycloprop[e]azulen-4-ol | 1587 | 1587 | 0.766 | - |
| 35 | (1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo [9.1.0]dodeca-3,7-diene | 1606 | 1605 | 0.749 | 0.093 |
| 36 | (1aR,4S,4aR,7R,7aS,7bS)-1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-4-ol | 1608 | 1607 | 0.624 | - |
| 37 | (E-)-Farnesene epoxide | 1624 | 1624 | 0.376 | - |
| 38 | Benzyl Benzoate | 1753 | 1753 | - | 0.17 |
| 39 | [3R-(3α,4aβ,6aα,10aβ,10bα)]-3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-1H-Naphtho [2,1-b]pyran | 1989 | 1989 | 0.202 | 0.081 |
| 40 | 1,4-Butanedione, 1,4-diphenyl- | 0.188 | 0.41 | ||
| 41 | 1-Pentyn-3-ol, 1,4-diphenyl- | - | 0.15 |
Table 3.
Chemical components of C. verum bark EOs from different cultivation locations.
| Components No. | Components | RI (Ref.) | RI (Exp.) | % EOs from C. verum Bark from Thai Nguyen Province | % EOs from C. verum Bark from Yen Bai Province |
|---|---|---|---|---|---|
| 1 | Benzaldehyde | 966 | 966 | 7.350 | 3.574 |
| 2 | Benzeneacetaldehyde | 1049 | 1049 | 1.447 | 2.667 |
| 3 | Acetophenone | 1068 | 1067 | 0.295 | 0.113 |
| 4 | Benzenepropanal | 1170 | 1169 | 1.857 | 1.093 |
| 5 | (Z)-3-Phenylacrylaldehyde | 1223 | 1224 | 4.003 | 1.345 |
| 6 | (E)-Cinnamaldehyde | 1266 | 1267 | 45.641 | 61.531 |
| 7 | Hydrocinnamic acid | 1361 | 1361 | 0.620 | 0.162 |
| 8 | 2-Propenoic acid, 3-phenyl- | 1434 | 1433 | 0.508 | 0.223 |
| 9 | (Z)-Cinnamyl acetate | 1445 | 1445 | 10.123 | 15.512 |
| 10 | (E-)-Cinnamyl acetate | 1452 | 1453 | 0.437 | |
| 11 | trans-Cinnamic acid | 1454 | 1455 | 31.709 | 2.022 |
| 12 | Cis-Cinnamic acid | 1463 | 1464 | 1.456 | 6.401 |
| 13 | (3-Phenyloxiran-2-yl)methyl acetate | 1502 | 1502 | - | 0.126 |
| 14 | 3-(2-methoxyphenyl)-2-propenal | 1505 | 1505 | 0.099 | - |
| 15 | Tetradecanal | 1606 | 1607 | 0.110 | |
| 16 | (E)-3-(2-hydroxyphenyl)-2-propenoic acid | 1630 | 1631 | 3.861 | 0.232 |
| 17 | Chalcone | 1970 | 1971 | 0.202 | 0.118 |
| 18 | 1,4-diphenyl-1,4-butanedione | - | - | 1.230 | 0.595 |
| 19 | 5-Phenyl-2,4-pentadienophenone | - | - | 0.114 | 0.105 |
| 20 | α-Oxo-benzeneacetonitrile, | - | - | 0.3001 | 0.177 |
| 21 | Trans-cinnamate vinyl | - | - | 0.208 | - |
Table 4.
Anti-microbial activities of C. verum bark EOs extracted by water distillation method. The values represent the averages of three replicates and statistical differences are considered at p-value < 0.05.
Table 4.
Anti-microbial activities of C. verum bark EOs extracted by water distillation method. The values represent the averages of three replicates and statistical differences are considered at p-value < 0.05.
| Bacterial Strain | MIC (μg/mL) | ||
|---|---|---|---|
| Thai Nguyen Sample | Yen Bai Sample | Ampicillin | |
| B. subtilis ATCC 6633 | 127.5 ± 11.5 | 114.5 ± 10.4 | 0.78 ± 0.08 |
| E. coli ATCC 25922 | 135.4 ± 8.3 | 115.6 ± 10.5 | 1.12 ± 0.1 |
| S. lutea ATCC 9341 | 124.4 ± 9.3 | 125.8 ± 9.5 | 1.23 ± 0.2 |
| L. plantarum | 146.7 ± 12.5 | 128.3 ± 10.5 | 1.78 ± 0.2 |
Table 5.
Anti-cancer activities of C. verum bark EOs extracted by water distillation method. The values represent the averages of three replicates and statistical differences are considered at p-value < 0.05.
Table 5.
Anti-cancer activities of C. verum bark EOs extracted by water distillation method. The values represent the averages of three replicates and statistical differences are considered at p-value < 0.05.
| Cancer Cell Lines | IC50 (μg/mL) | ||
|---|---|---|---|
| Thai Nguyen Sample | Yen Bai Sample | Ellipticine | |
| HepG2 | 18.5 ± 2.5 | 23.5 ± 2.25 | 1.11 ± 0.45 |
| MCF-7 | 17.5 ± 1.5 | 28.5 ± 2.55 | 1.34 ± 0.50 |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
MDPI and ACS Style
Phu, H.H.; Pham Van, K.; Tran, T.H.; Pham, D.T.N. Extraction, Chemical Compositions and Biological Activities of Essential Oils of Cinnamomum verum Cultivated in Vietnam. Processes 2022, 10, 1713. https://0-doi-org.brum.beds.ac.uk/10.3390/pr10091713
AMA Style
Phu HH, Pham Van K, Tran TH, Pham DTN. Extraction, Chemical Compositions and Biological Activities of Essential Oils of Cinnamomum verum Cultivated in Vietnam. Processes. 2022; 10(9):1713. https://0-doi-org.brum.beds.ac.uk/10.3390/pr10091713
Chicago/Turabian StylePhu, Hiep Hoang, Khang Pham Van, Thien Hien Tran, and Dung Thuy Nguyen Pham. 2022. "Extraction, Chemical Compositions and Biological Activities of Essential Oils of Cinnamomum verum Cultivated in Vietnam" Processes 10, no. 9: 1713. https://0-doi-org.brum.beds.ac.uk/10.3390/pr10091713
Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.
